Dimethylformamide → HCID 25150126, compound

HRID 2108620Notes

Reaction equation

HRID 2108620 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:24])[CH:5]=[C:6]([CH3:23])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12](COCOC)=[C:11]([CH:20]([CH3:22])[CH3:21])[CH:10]=1.[C:25]([O-:28])([O-])=[O:26].[Cs+].[Cs+].[Br:31][CH2:32][CH2:33]Br.[CH3:35]N(C=O)C>C(OCC)(=O)C>[Br:31][CH2:32][CH2:33][O:24][C:4]1[CH:5]=[C:6]([CH3:23])[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:26][CH2:25][O:28][CH3:35])=[C:11]([CH:20]([CH3:21])[CH3:22])[CH:10]=2)=[C:2]([CH3:1])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 66642769HCID 66642769, compound

Product 1

HCID 25150126HCID 25150126, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxymethylbenzyl)phenol (1.00 g, 3.18 mmol, Chiellini et al., Bioorg. Med. Chem. Lett. 10:2607 (2000)) in DMF (30.0 mL) was added Cs2CO3 (5.18 g, 15.90 mmol) followed by 1,2-dibromoethane (1.64 g, 19.08 mmol). The reaction mixture was stirred at 60° C. for 2 d, diluted with ethyl acetate and washed with water (20 mL×4) and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:19) to afford 1-(2-bromoethoxy)-4-(3′-iso-propyl-4′-methoxymethoxybenzyl)-3,5-dimethylbenzene as an oil (0.26 g, 16%): 1H NMR (300 MHz, CDCl3): δ 6.94 (m, 2H), 6.67 (m, 3H), 5.18 (s, 2H), 4.32 (m, 2H), 3.95 (s, 2H), 3.68 (m, 2H), 3.51 (s, 3H), 3.37 (s, 3H), 3.32 (m, 1H), 2.26 (s, 6H), 1.22 (d, J=6.0 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-ethyl acetate (4:1); Rf=0.91.

Workup

  1. washwashed with water (20 mL×4) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate-hexanes (1:19)

Sources & evidence

ORD record
ord-13faac2605dc49748175c73f281fc5f0
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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